Water → HCID 67296090, compound

HRID 2276856Notes

Reaction equation

HRID 2276856 reaction equation
[C:1]1([C@H:11]([NH:13][C@H:14]2[CH2:18][CH2:17][C@@H:16]([C:19]3[CH:28]=[CH:27][C:22]([O:23][CH2:24][C:25]#[N:26])=[CH:21][CH:20]=3)[CH2:15]2)[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Cl-:29].[NH4+].[N-:31]=[N+:32]=[N-:33].[Na+].O>CN(C)C=O>[ClH:29].[C:1]1([C@H:11]([NH:13][C@H:14]2[CH2:18][CH2:17][C@@H:16]([C:19]3[CH:20]=[CH:21][C:22]([O:23][CH2:24][C:25]4[N:31]=[N:32][NH:33][N:26]=4)=[CH:27][CH:28]=3)[CH2:15]2)[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 67296164HCID 67296164, compound

Product 1

HCID 67296090HCID 67296090, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Under a nitrogen stream, {4-[(1R,3S)-3-{[(1R)-1-(naphthalen-1-yl)ethyl]amino}cyclopentyl]phenoxy}acetonitrile (150 mg, 0.40 mmol), ammonium chloride (325 mg, 6.1 mmol) and sodium azide (263 mg, 4.0 mmol) were suspended in N,N-dimethylformamide (3 mL), followed by stirring for 3 hours at 80° C. The reaction solution was cooled to room temperature, followed by addition of water, and the precipitated powder was collected by filtration and washed with ethyl acetate to give the free form of the title compound (100 mg, 60%). The free form obtained was converted to the hydrochloride using 0.5N hydrochloric acid/dioxane.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. filtrationthe precipitated powder was collected by filtration
  3. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-42e148e860b1412ba9929dba5e26f2d5
Source dataset
uspto-grants-2015_09
Patent number
US09133140B2

Reaction notes

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